Hydrochloric Acid → (+-)-4-Ethyl-4-[(tosyloxy)methyl]-2-oxazolidinone

HRID 853

Reaction equation

HRID 853 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].C([N:14]1[CH:18]([CH2:19][OH:20])[CH2:17][O:16][C:15]1=[O:21])C.Cl.N1C=CC=[CH:25][CH:24]=1>[Cl-].[Na+].O>[CH2:24]([C:18]1([CH2:19][O:20][S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:3])=[O:2])[CH2:17][O:16][C:15](=[O:21])[NH:14]1)[CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 19694098(+-)-Ethyl-4-(hydroxymethyl)-2-oxazolidinone

Product 1

HCID 18968885(+-)-4-Ethyl-4-[(tosyloxy)methyl]-2-oxazolidinone

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Tosyl chloride (142.2 g, Aldrich) was added to an ice-chilled solution of the product from step (a) (102.7 g) dissolved in pyridine (175 ml. Aldrich). The reaction mixture was stirred at ice bath temperature for six hours, then allowed to come to room temperature. The heterogeneous mixture was added to 1500 ml of a solution of brine and 1N HCl, stirred until solids appeared, filtered and washed with diethyl ether to give 194.6 g of a beige solid as the title product. 1H NMR consistent with the proposed structure.

Workup

  1. customto come to room temperature
  2. stirringstirred until solids
  3. filtrationfiltered
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-85a305aeebfc4263a0d5dfa4da2ff2f2
Source dataset
uspto-grants-1998_03
Patent number
US05723458

Linked notes

Loading…